Toluene → HCID 57457834, compound

HRID 1469324Notes

Reaction equation

HRID 1469324 reaction equation
[NH2:1][C:2]1[CH2:3][N:4](NCC2(O)CCCC2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([O:27][CH2:28][CH3:29])(OCC)OCC.Cl.[N:31]1[CH:36]=CC=C[CH:32]=1.[C:37]1(C)[CH:42]=CC=C[CH:38]=1>>[N:31]1([CH2:36][C:28]2([OH:27])[CH2:29][CH2:42][CH2:37][CH2:38]2)[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:32]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 31214Ethyl orthoformateHCID 10176127Pyridinium chlorideHCID 66919169HCID 66919169, compound

Product 1

HCID 57457834HCID 57457834, compound

Procedure

A mixture of 1-{{(3-aminoquinolin-1-yl)amino]methyl}cyclopentanol (2.00 g, 7.8 mmol, Example 3 Parts A through D), triethyl orthoformate (1.36 mL, 8.2 mmol), pyridine hydrochloride (0.2 g), and toluene (20 mL) was heated at reflux for 3.5 hours. The reaction mixture was allowed to cool to ambient temperature. A solid was isolated by filtration and dried. The solid was triturated with a minimum amount of saturated aqueous sodium bicarbonate for 1 hour. The solid was filtered and then dried to provide 1.85 g of 1-[(1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclopentanol as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. customA solid was isolated by filtration
  4. customdried
  5. customThe solid was triturated with a minimum amount of saturated aqueous sodium bicarbonate for 1 hour
  6. filtrationThe solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-4230cf5e624f4c5eaee907c8b12a4866
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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